Trifluoroacetic acid → 4-(4-(5-fluoro-2-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)cyclohex-3-enone

HRID 528007Notes

Reaction equation

HRID 528007 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]2[C:9]3[CH:16]=[C:15]([C:17]4[CH2:26][CH2:25][C:20]5(OCC[O:21]5)[CH2:19][CH:18]=4)[NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]2[C:9]3[CH:16]=[C:15]([C:17]4[CH2:26][CH2:25][C:20](=[O:21])[CH2:19][CH:18]=4)[NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 904182984-(5-fluoro-2-methoxyphenyl)-6-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 904185524-(4-(5-fluoro-2-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)cyclohex-3-enone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of Example 83A (370 mg, 0.970 mmol) in 15 mL dichloromethane was added excess trifluoroacetic acid. The reaction was held at room temperature overnight. The volatiles were removed in vacuo, and the residue was dissolved in 30 mL ethyl acetate. The mixture was washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, and concentrated to give the title compound. MS (ESI+) m/z 338.2 (M+H)+.

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe residue was dissolved in 30 mL ethyl acetate
  3. washThe mixture was washed with saturated sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6956bb5755394ef39aba88a9bc0224b5
Source dataset
uspto-grants-2016_05
Patent number
US09346813B2

Reaction notes

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